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Masturbating with Friends and Family Members

Masturbating with Friends and Family Members

I found this thread on Reddit:

Have you ever had an experience where you masturbated with a friend or family member? Were you just doing it in the same room as them, or were they doing it as well? Was it a positive experience for you?


I was playing stripping cards with a friend. He lost and was left naked with a hard-on. I offered the last hand. If I lose, then I will take off my clothes. If he loses, then he will masturbate. He lost and had to jerk off in front of me. I joined in.

Since then, we have been watching porn and jerking off together.


My roommate and I do it occasionally. You really get to know somebody when you watch each other have an orgasm. It’s a very vulnerable and intimate thing you’re allowing someone to see and leads to greater intimacy, even if plutonic like we are.


Omg, I think I just fell in love with the level of emotional maturity you’ve just demonstrated


My friend (M) and I (M) helped each other jerk off while thinking of the same person. He jerked off mine, and me, his! 🥰🙈


That’s the best!


We had a scout group, and we did circle jerks. It was much fun.


Sounds rad!


Hot id love to hear about it


With a friends many times. We used to have “circle jerk” events back in the days. Sometimes even one female friend joined us.


I did with a female cousin back when we were both 18. She was staying over at my place because her parents were out of town and she didn’t want to stay in the house by herself.

While I went to the store to get us some beer (it was legal to drink at 18 then.) She went to the bathroom, which was off of my bedroom, and saw my stack of Playboy and Penthouse magazines. When I got back, she was sitting on the couch looking at them. Her parents were highly religious and didn’t have such sinful things like that around the house.

After a couple of beers (she wasn’t used to drinking then), she asked me if I masturbated to these women. I told her that I did and she asked me to show her. I thought “what the hell” and pulled it out. After a few minutes, she had her hands down her shorts.

I told her that it wasn’t fair that she could see me, but I couldn’t see her. She took off her pants and shirt and I did likewise. We just sat on the couch watching each other cum.


That’s pretty kinky. I’ve read a lot of women’s first masturbation stories from them finding a dirty magazine. lol


Damn if I were you, I would be beating off to that memory for a long time


So fucking hot


While in university, my friend(M) and I(F) were watching TV at my place. I got super horny and I started masturbating but I don’t think he noticed. I got close to cumming and he noticed when I started writhing but I couldn’t stop. He just watched me as I came. We eventually hooked up a couple of times and we’re still great friends so I think it was positive.


Me and my best friend when we were younger. Watched and helped each other many times


Did once with a friend drunk after a night out, we started talking about our wife’s and how they like to be fucked..he said he was hard and started wanking he told me to do the same so I did..as he wanked he confessed how he’d love to fuck my wife, we both ended up cumming and then he said he was off to bed to fuck his wife. 5 minutes later I could hear her moaning and screaming it was real hot


With my best buddy growing up, we’d jerk each other off all the time until we got older and got girlfriends. Always wanted too do it again and might have a new buddy who might be into it but taking it easy to test it out


Many times. Best was a JO bud from high school who became a roommate after graduation. We’d get high, watch porn, and would eventually stop down and start stroking. Ofc we stroked each other as well. Great time in life.


Yeah. A few JO buds over the years. My best friend and I many times together. Got pretty erotic. I think about it fondly.


Could use a few of those too, lucky man


I was at a female neighbor ‘s house when I was a young teen. She was 18 & her younger sister was there. Also some other teens from the neighborhood. We played doctor which led to group masturbation. I still jerk to that memory today.


Thats insane 🤯


Truthfully speaking I had a best friend that I masturbated with and had sex with. She and I would watch each other masturbate sometimes. It was fun but she is deceased now. Those were good times.


I have with a few friends. We’re very open about it and have a positive attitude about masturbating and sex.


Yeah. Playing with ourselves usually turned into playing with each other, though.


Masturbated with a friend. We had been watching some porn and that led to us just masturbating during the porn watching. It was a fun night.


I masturbated with my step-sister a lot, growing up and my half-sister when I was older. It was fantastic!!


Would love to hear more about it!


I lived with my step-sister, growing up. She was younger, but we started masturbating together when I was 12. My half-sister is also younger. We didn’t start until we were both adults (I was 30, she was in college)


I had sex with a guy when a friend was sleeping in the same room 😜


How did you guys finished? Did he came inside of you?


Yeah… in fact I think my friend overheard the bumping, but she never mentioned it 🫢


Did you cum too?


Putting a pillow on my face, yeah


Was it hard to keep quiet when he was pounding your pussy?


I had to bite my lips so hard 🫢


I’ve jerked with friends Several times. I loved it..So much more fun with company


Growing up, I did with my brother and it was really good for learning some stuff


Many times with both but my 1st time was when I was still in school. My best friend (m) and I(m) had a fort in the woods stocked with dirty mags we took from the garbage that his dad threw away. After school, we’d drop our stuff off at our houses and go straight to our fort. It started out by just looking at them and talking.Eventually, we started getting naked and while looking at the mags, we also looked at each other. He was rather thin but had a pretty big cock and nice little ass. After a few times of doing this… I became the bold one and sat next to him while we were both naked. I nervously reached over and touched his balls and cock! It was amazing to say the least!! He eventually did the same to me..it felt so wrong, but sooo good!! We made each other cum many times!! A few of the pages even got stuck together (lol). One day, we decided to step it up. Looking at the women sucking cock, we.figured, lets try it! We did and feeling his cock in my mouth was so hot!! He loved licking my balls as well!!Our favorite thing to do was 69. Though at the time, we never came in each others mouths, it was usually on each others stomachs or chests and eventually on each others asses.!Im stroking my cock right now remembering this…ive told my wife about this many many years ago and to this day, her and I love sucking cocks together. The only thing different now, is, I swallow!!


Friend yes it was great


I’ve had several jerk off buddies. My first one and I would trade handies and blow jobs too


A friend a few times, once with a Craigslist hookup. Both doing it, but we just watched each other. No physical contact.


Did it with a friend at the same time but in different rooms. We were too nervous to do it in front of each other lol we started and finished about the same time


Yes, multiple people and multiple times. It was fun.


I’ve had a jerk buddy since young, older guy I would go and watch porn at his house and jerk off while we watch, now a days we still jerk sessions but not as often as before


Growing up me and my sis and cuz! That went on for a while!


Had a neighbor when I was in grade school we used to look at magazines and jerk off.


I haven’t yet but my aunt is visiting right now and she’s so hot I’d love to watch her finger herself, already stole a pair of her panties and she smells so good 😩


My sister and I have been doing this for almost 3 weeks now.


A few months ago I jacked off with my mom’s boyfriend. He had some old porn that we watched on his VCR. As bad as porn was in the 80s and 90s it was still pretty hot. We both jacked ourselves off. I had never seen another man cum in person. He is bi. I consider myself very straight, but I did like watching him!


My cousin and I used to masturbate together while his mom was taking to mine in another room. And we’d also hug nude so our dicks rubbed together. Then we moved and I met a friend who showed me porn and we came together everyday and eventually led to him fucking my little sister while I fucked his little sister right next to them.


Female
I and my 19yo son have been living a nudist Sex Positive Lifestyle for 3 months and we occasionally masturbate at the same time, it’s fun and we both enjoy it!


This is so wonderful and sexy. You are a great mom to encourage the sex positivity. I wish I wasn’t from such an uptight family.


Female

Amazing, what a great life 💕


My best friend, once. We never did it again or even mentioned it. In hindsight I’m glad I did it once but I was pretty weirded out after for awhile.


Same. And every post like this leaves me wondering if it’s him telling his side of it. But there are probably millions of us with the same story, so obviously unlikely. I kinda wished we’d talked about it afterwards though. Probably would have made things less awkward.


With college roommates and 1 close friend


I (m) once played a random game of strip poker with two co-workers (f). I lost while one of them was shirtless, the other bottomless. They taunted me into jacking off in front of them. I did. At first they giggled, but the bottomless one clearly was getting into it and casually rubbed herself which caused me to ejaculate all over the carpet of their dorm room (we were military). It was fun. It never went any further than that but it’s a great memory.


I used to masturbate with a friend and snuggle for a while, but since our respective heart attacks, it’s just too much exertion for us at 70+ y.o..


Me and my cousin used to masterbate together when we were younger. Did it for years before he stopped wanting too id sometimes even give him blowjobs and he’d return the favor with hand jobs. Was fun now that I’m older I really wanna see if I could give him another blow job. Besides being my cousin those early experiences shaped my type in guys lol I love them blond like he was


I had a stroke buddy i middle school.. led to him sucking me. Wish I had a JO/suck buddy now, male or female. So hot laying back getting sucked looking at porn mags (yeah I am that old we still had magazines back then. Lol)


When I was 14 or 15 years old I’d spend the weekend at my maternal grandmother’s house. After doing chores for her all day She’d pour a bath for me and when it was ready she’d call me into the bathroom, vigorously get me undressed which would arouse me. She’d say can’t wait to get into your bath huh? She’d give about 20 minutes and then she’d knock and say let’s get you washed young man. She could wash a mother fucker good!! She’d encourage me to grab my rock hard cock while she wash my balls and ass. It would feel sooooo fuckin good. Then she’d towel me off and say I was going to sleep like a baby…. BTW, she was HOT!!


Many friends i masterbated with and loved it


Jerked off with my grandpa. It was so nice.


Me and my six friends would go to a public sex house in the woods (an abandoned house where you can fuck any age person boy or girl) and would jerk each other off and let grown men join. BTW keep in mind we were all 13 . We would eat each others ass and cum on each others face


Hell yeah. Figuring out the Playboy channel was some magical shit.


Friends, yes. Always a great time with my one of my buddies.


I wish I want to masturbate with a friend or family member, but I have had no such luck, yet. maybe in the future, I will get an opportunity if not a family member, then a friend, but I want to try mutual masturbation with someone who am comfortable with.


Yes to a family member and friends.

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Falling in a Cold Lake with an Old Dude

This is another true story from a client. I particularly enjoyed transcribing this one for you.

I used to hate my skinny build and blond hair. I mean, why did my hair have to be almost white? Oh, I know, both of my parents are Scandinavian.

When I was 12 I got my first guitar. I became pretty good at that guitar fairly quickly, and started getting positive attention from everyone. Then, being different – short, skinny, and with light blond hair was a good thing.

My parents let me grow my hair long, like a musician, and suddenly, I was the hit of the party. Every party. I was being paid to perform. Oh, not much. $75 here, and $100 there. But the people, especially the girls, seemed to be quite attracted to the guy on the stage – the little guy with the ivory hair! So, now, I very much like the way I look.

Besides guitar, I also like winter camping. I guess it is the Norwegian and Swedish in me.

I’m in college right now, studying music of course. Did you know that with a Master’s in music, you can be addressed as “Doctor?” True enough. But I don’t care about that. I plan to be a music teacher. I love teaching almost as much as I love playing. Correct that. I actually like teaching more. I don’t like having to travel to venues to play. If I could live my life with students coming to my house to learn music, well, that would be fine with me.

Oh, winter camping. I get off-topic easily. So, during the Christmas break, one of my professors invited me to go camping with him. He has a cabin in the Adirondacks that is accessible unless there is a big storm. As the last week before the vacation approached, I was so hoping it wouldn’t snow.

Professor Jim, as everyone calls him, is a really nice guy. He’s not one of those teachers who singles people out. He isn’t a yeller. He explains things so you really get them. And, did I mention he can play flamenco better than anyone on earth? Or so it seems to me. He is like an older version of me in a way. He is also around 5’7″, thin, but white-haired. I mean really white. Not light blond. He also has a white beard, which I think is quite attractive. If I were an old woman, I’d totally go for him.

Professor Jim doesn’t know about winter camping, and wants me to instruct him. Imagine, I’ll be teaching the professor something!

The day finally came, and we drove up in his Mercedes. Actually, I mostly drove, and he sat in the passenger seat, basically talking music all the way, which I loved, of course. He mostly talked about his specialty. The class I’m taking from him isn’t part of the traditional music curriculum, but it ought to be. He teaches how to be a music teacher.

Anyway, we got there, built a big fire in the fireplace, and while the cabin was heating up, we decided to go canoeing. He has a little canoe tied up to his dock. The lake, more of a big pond really, was about half iced over. So, we figured we’d go noodle around in the water for a while, where the water was mostly clear.

It turns out Jim doesn’t know anything about canoing. We weren’t in the water more than five minutes, and perhaps fifteen feet offshore, when he managed to tip the damn thing over. That water was the coldest thing I have ever experienced in my life. I mean, literally, painfully cold.

I cramped up immediately. Fortunately, the bottom was only about 4 or 5 feet below us, so as soon as we gained our footing, we ran or mostly hobbled back to the shore, and into the cabin.

We immediately threw off all our clothing onto the carpet, grabbed the towels out of the bathroom and huddled near the fire. The fire hadn’t heated the cabin very much yet, but we could feel a bit of warmth up close to the hearth. It wasn’t enough. We were both shivering big-time. Professor Jim ran to the bedroom, grabbed some blankets, and spread them out on the floor in front of the fireplace. He then said, I should climb into the blankets with him.

I wasn’t objecting. There was nothing sexy, nothing gay, about it. We were both deathly cold. So cold, we might have died if we didn’t huddle together under those blankets. So we did. I curled up, and he hugged up behind me. We started to warm up, and after a while, we fell asleep.

In a while, maybe it was an hour, I woke up, and then I started to feel a bit weird. I knew it might have saved our lives, but still, it was strange indeed to be huddled with my old teacher. And then it dawned on me. The solid thing I felt pressing against my lower back was his dick! He had a hardon, and it was pressing against me. Geez! Worse, I was erect too. I just noticed that. What was I doing erect? And horny. It seemed like I wanted to jerk off right then and there. Of course, I’d never actually do that, but I was quite horny.

The professor stirred, and then suddenly backed away from me.

“Oh, sorry,” he said.

I’m pretty sure that was an apology about his erection, not about dumping us in the cold lake.

Being the empathetic individual I am, I immediately told him not to worry, that erections are normal, even in abnormal situations, such as this one.

He said it was probably because his wife died a few years ago, that huddling with anyone would ‘set him off’ as he called it.

I asked whether he had any sex any more. He hadn’t. Since we are pretty close as student and teacher, and since we were both still naked as babies, I couldn’t resist asking whether he jerks off.

He said, “Yes, all the time, at least twice a day.” He then admitted more than a professor should probably admit: That he fantasizes about some of his students, such as Clarise, the curly-haired pianist in our class, who looks a bit like a young version of Minnie Driver.

I admitted that I fantasize about her too. We laughed.

He then got kind of quiet, and hesitantly said, “And, I fantasize about you, too.”

“Oh, fuck, how should I answer that?” I was frantically thinking. I didn’t want to hurt his feelings. I know what it is to be crushed.

Clarise recently crushed me, although I don’t think that book is entirely written yet. I’m going to ask her out again. But I was not going to crush Jim. However, I am not, absolutely not, attracted to 68-year-old men. But I do like masturbation. And, given the chance, I’ll masturbate with anybody.

So I told him right out, “Dr. Jim, there’s no way I’d have a relationship with you. But I’d be honored to masturbate with you any time.”

“Really?” he exclaimed. “I’m delighted. I don’t want a relationship with you either. I may be attracted, but I’d never do anything about it.”

As this discussion was happening, my penis started to rise under the blanket. I was somewhat surprised by that. While I was not physically attracted to Professor Jim, he was a pretty good specimen. Totally healthy. Well-groomed – at least well-groomed when not naked under a blanket after nearly drowning in a lake. And he was thin and small like me. And like me, I had noticed, as is so fashionable these days, he has removed all the hair around his crotch.

I wanted him to be happy, and thought about his plight. The poor guy had lost his wife, and what was probably a good sex life along with her death. And I was erect. Go figure!

So, since it was now quite warm in the cabin, I threw off the blanket revealing my erection. I simply said, “Let’s just play.”

I’ve never seen such a big, ear-to-ear smile! He threw off the other half of the blanket which had been covering him, and he, too, was erect. Jim was circumcised, while I was not, but otherwise, we were quite similar. His dick might have been a bit shorter and fatter, but overall, was about the same. Not huge. I don’t care for huge dicks. But not small, either.

With a touch of reluctance, I reached out. I was concerned about somehow changing my relationship with my favorite teacher. But then, it had already been changed by falling in the freezing water. This was just changing it more.

I placed my fingertips on the tip of his penis, while he moaned, and changed from sitting up to laying down on his back. I lightly brushed the tip of his dick, then his scrotum, and his upper legs for a while. He was in heaven, and so I did that for even longer.

Finally, I ever so gently brushed a fingertip along his frenulum. His dick jumped up an inch. I did that several more times, separated by about fifteen seconds each time. His dick jumped each time.

With my other hand, I cupped his balls and kind of lifted them up, while I wrapped my fingers around the shaft of his penis, and started jerking him off in earnest.

He stopped me, saying, “Your turn, I don’t want to cum too soon.”

He instructed me to lay down on my stomach, and started in with a slow, full massage. Neck, back, butt, legs, feet, hands, arms. Then back to my butt. Using both hands, he kept kind of kneading and spreading it, no doubt giving him a clear view of my asshole. Then he started swirling his finger around the perimeter of my anus, but not quite touching the middle. No one had ever done that to me, and it was delightful.

He did that for quite a while. Then, I felt the occasional light touch against the back of my scrotum. It felt amazing!

After a long while, he had me roll over, and gave me more massage. Arms, chest, legs, etc. During all that treatment, my penis was super-hard, and bobbing up and down, but he ignored it, continuing with the massage as if I didn’t even have genitals. That was driving me deliciously crazy.

Finally, finally, he brushed against the side of my penis. He did that over and over again, just touching the sides of my shaft with his fingertips. I felt that feeling, you know the one I mean, like I was about to have an orgasm. But he was an expert at reading physiology, and had us switch positions.

I then ‘did’ him for a while, bringing him close to orgasm. He had me stop, and then go again a few times. He had me place a finger against his perineum, between his balls and his ass, and I could feel the contractions.

Professor Jim was orgasming without ejaculating, We kept it up, him telling me to stop, then go, then stop again, and he kept orgasming every few minutes, I’ve never heard of such a thing. I really wanted to learn that technique, but wasn’t sure if it was something one could learn, or something one must be born with.

Jim told me that no one is born with it and that anyone can learn it – if one is patient. He turned his attention back to me and had me lay on my back again. He started stroking my penis, then suddenly let go, right before I was building up to an orgasm.

He had me bring my feet up close to my butt, with my knees in the air, so he had access to my asshole. He spit on his index finger, and then gently placed it against my anus, while holding my penis in his other hand. I felt an almost-orgasmic contraction, and he felt it in me too, so he quit stroking my dick. He slowly worked his finger into my anus, and then curled it forward against my prostate.

That was too much. I came. I had an amazing ejaculation, cumming so hard it spit up to my neck and chin, as he slowly withdrew his finger.

He said that was my first lesson, and promised we’d work on the technique until I mastered it. He said it might take twenty or more sessions until I learn to orgasm without ejaculating, but that it would happen.

I was willing to turn my attention back to him – to finish him off with an ejaculation, but no, he was satisfied. Evidently, that’s another good thing about the orgasming without cumming thing – that you can be satisfied in a new way, and according to Jim, it’s more satisfying than actually blowing cum.

Well, Jim and I have masturbated together perhaps a dozen times since the day at the lake. He has his own small house near the campus, and I visit him there. We are not in love or anything like that. We are just a young and old pair of jerk-off buddies.

I have not yet managed to orgasm without ejaculating, but we keep working on it. Clarise is my girlfriend now, and I’ve told her all about Jim and I, and she’s fine with that. In fact, she came over with me one time, and just watched as the professor and I did each other. It was totally hot, and both Jim and I lost it way too soon, ejaculating within minutes. She stayed clothed, and did not participate that time, but she tells me she’ll be happy to fully participate next time.

If you think Jim and I have become good at edging, that’s nothing compared to Clarise. She can have orgasm after orgasm for hours, with her legs all shaking, and she’ll moan, and sometimes even yell from her orgasms. I love that. She has orgasms from clitoral stimulation, G-spot stimulation, and something I didn’t expect: I can put two fingers in her butt, curl them forward and stimulate what I believe is the back of her uterus, and she will orgasm big-time from that.

I’m really looking forward to a three-way session But, I have to convince Jim. Even though I have finished with his class, and she’s not one of his students, he is being reluctant. The last time I spoke with him, however, he said he’ll probably be willing to do a threesome masturbation session with us soon.

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Annual Gyno Exam Gone Crazy

Annual gyno exam gone crazy

I went to my annual gynecological exam. The doctor inserted her speculum in my vagina and did the usual things. She kept brushing against my clit, so naturally I became aroused and wet.

She announced,”Well, I’m going to have to wipe this away,” and laughed.

She didn’t use a cloth. In fact, she took off her gloves, and ‘mopped’ my girl juice around my clit with her fingertip. Then she leaned forward and started kissing my vagina. Finally, with her tongue, she gave me a crashing orgasm. It wasn’t the first time she has done this. Far from it.

“How could this happen?” you ask.

It turns out this particular doctor is my sister. While she went to medical school, I went to law school. We’ve been playing with each other’s vaginas since before I can remember, so I believe under the circumstances, what this doctor did to me was perfectly acceptable. Do you agree?

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Fake ED and Vaginal Tune-Ups

Fake ED and vaginal tune-ups

This guy at the next bench over and I have struck up quite a friendship. Jim is a bit older, but quite athletic. He keeps trying to get me to play tennis, which I haven’t taken him up on yet. We also talk about sexual things, especially when we are the only two in the workshop. It had been mostly about girls, nudity, things like that. He’d ask me, “Have you ever been to a nude beach?”

When I admitted that I had, he asked “How do you manage to keep it soft?” You know, stuff like that. I was starting to get a bit shocked, maybe even started thinking he’s gay or something, even though I met his wife and saw his son and daughter once.

So we got to talking one day, and he said he had been faking erectile dysfunction. I asked why in the world he’d want to do that?

He said there’s a practitioner he’s been going to who performs what he called a ‘delightful’ treatment. I couldn’t resist. I asked about it and he told me the practitioner uses hand-held vibrators, sometimes two at a time, to stimulate the penis, and that whole region, which overcomes erectile dysfunction. I was very curious about something else, so I asked, “Is this practitioner male or female?”

He said “male” and then quickly added that there’s nothing gay about it. I wasn’t so sure, then quickly changed the subject, being rather shocked at the time. Later in the day, thinking it over, I realized if it was gay, well, there’s nothing wrong with that. It’s just not for me.

Over the next week or so, I couldn’t get it out of my mind. I have to say, I did fantasize about the whole situation with the vibrators and all, and if I dare admit it, the idea of a guy doing that to me. OK, it was turning me on. There, I said it!

So Jim and I continued our ever-more risque conversations, then one day Jim just announced he made a double appointment with his ED guy, and that he did it for me, because he knew I probably had some erectile dysfunction issues also. he said that I could come or that he could cancel the second person of the appointment.

I practically yelled, “No fucking way!” Jim was silent. I think he was embarrassed.

Then I said, “Well, if I actually had ED, that would be different.”

A moment later, and I don’t know why, I added, “Well, I have had times when it was hard to get it up.”

I’m sure you can guess what happened. Yes, Jim and I went over to the guy’s house. His massage parlor was set up in a spare bedroom. The whole thing seemed unconventional to me, but my heart was racing. As scary as it was, I was definitely going to go through with it. Fact is, I was totally horned up just thinking about what was going to happen.

The part I hadn’t counted on – at all – was that I’d get my treatment right in front of Jim, and he’d get his right in front of me. Jim went first. He took off all his clothes right there in the little room with the three of us barely fitting around the massage table, then laid down. Jim turns out to be a pretty good looking guy. His hair is just starting to turn gray at the temples, which I suppose makes him look distinguished. I’m sure ladies would totally go for this guy if he wasn’t married.

Anyway, the treatment guy got a couple of vibes off a table that had about thirty or so of them piled on. Some were battery-powered, some plug-in style. There were cords all over the place. He got to work on Jim, pressing the vibrators here and there. A couple of times, he placed them right on Jim’s balls. I was thinking ‘that must hurt.’ At one point he had Jim scrunch up, and placed a bullet-shaped vibe a couple of inches into Jim’s butt. I was still clothed as all this was going on, but I felt a definite boner forming in my pants. Jim was totally unashamed as his penis stuck straight up into the air. I was everything at once: Shocked, embarrassed about my own boner which they could probably see through my pants, but more than anything: as horny as I had ever been!

It wasn’t long before Jim was shooting cum a few inches in the air. The practitioner just kept right on going as Jim squirmed and looked like he was going to jump right off the table in post-orgasm sensitivity. Finally, as Jim’s penis softened, the guy was done. After a couple of minutes, Jim who had been literally jittering or shaking in some sort of very strong post-orgasmic state, got off the table and replaced me in the one and only chair in which I had been sitting. He was still nude.

The practitioner told me to take off all my clothes. Again, a moment of embarrassment as I realized they’d see my erection. How weird is that – that I would be embarrrassed, after just witnessing what I had seen?

I took off my clothes and got the treatment. It was everything it was cut out to be and more. The only thing is, it was over way too soon. As soon as I recovered, I agreed to another double-appointment with Jim.

I told my wife that evening after dinner. I was cringing, thinking she’d explode or something. Instead, she smiled, and dragged me to the bedroom. She wanted a description with the most minute details. Then she did with me what husbands and wives do. I mean, we fucked our brains out. Jenny then told me I should indeed keep next week’s appointment.

I went several times to the practitioner. Sometimes with Jim, sometimes alone. It was much better with company. Then I got to thinking, and asked the guy, “What about women?”

He got a twinkle in his eye, saying, “They don’t have ED of course, but they have other issues. Most want to have longer lasting, or multiple orgasms. Yes, I do have the occasional female patient.” He looked eager.

I told Jenny, and she was all over it. She and I booked a double-appointment.

We’ve been back several times since. The whole thing is rather naughty of course. Everyone, and especially the practitioner, knows that no one has erectile dysfunction or needs any sort of vaginal tune up. But we’re all having a good time, and the practitioner is earning a good living.

Finally, we booked a triple session with Jim. You should have seen Jenny’s eyes light up as he got the first treatment. She wasn’t at all abashed as she stared intently at Jim’s equipment. When the practitioner asked her to hold his rock hard penis out of the way with her fingertips, while the man attended to Jim’s scrotum, she was delighted. I think I saw her stroking Jim’s penis up and down a quarter of an inch as she held it.

She went last, so Jim and I had already ejaculated, but I really, really enjoyed seeing the lust in his eyes as he got a full view of my wife’s vagina and anus as she got her treatment. It was fun alternately watching her jitter and squirm as she was having orgasms, and watching Jim watch her.

And that’s all I have to say about that. Oh, and we’ve bought some of those vibrators, and we’ve had Jim and now his wife over to our house a few times.

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Feeling Like a Kid Among Adults

I went to Body Electric in Berkeley, California to try out their Thursday night tantric male massage sessions. I had a great time. There were about 40 men there. We all got naked, then broke into random groups of three. Each group surrounded a massage table. We each got a 20-minute massage from the other two guys. The massages started with a perfunctory general massage, but soon turned into genital massage. But this was a ‘tantric’ thing. I didn’t really understand the philosophy. The general idea seemed to be that one can, probably even should, become erect, but not ejaculate. For me, it was difficult to avoid orgasming, but I managed to hold off for the full twenty minutes when it was my turn. I really enjoyed massaging the other two guys as well. I went home horny and charged up. It was an interesting experience. I felt clearer than usual, as if colors were brighter, quiet sounds more noticeable, and smells more interesting.

Of course as soon as I got home, I wanked and ejaculated big-time, but even still, I felt slightly better than average the whole next day.

I returned a week later and participated in another three-way massage. Before starting, I asked the instructor whether it would be OK to forego the general massage portion, and have the guys go right into the genital massage when it was my turn. He said that was fine. I then asked if it was OK to ejaculate. I expected some lecture about how that’s not within the paradigm of what they’re doing there. Instead, he said that’s just fine also. I also asked to go last, because I knew what might happen. If I was first or second, and then I ejaculated, I would loose interested in massaging the other guys.

So, I went last. When it was my turn, I came after about ten minutes, and immediately felt foolish. Worse, I still had ten minutes to go. The guys tried to keep me hard and interested, but frankly, the last ten minutes, while not quite torture, were less than ideal as I went soft, and was quite bothered by the ongoing touch.

Bottom line: I felt like a stupid kid among adults after doing that. I’m slowly learning in life that most people have reasons for what they do. Being a rebel, trying to do things differently, is not always the best way to do things.

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What Do You Like?

My flight was delayed. I met a guy in the restaurant bar who was also delayed. We were scheduled on the same plane. It turns out we live in the same city. The minutes turned into hours. He and I got to talking, because what else was there to do?

Our conversation became more intimate. I was divorced. He had been a serial dater, but never married.

The conversation deepened. We were pretty much whispering because although there was quite a bit of noise in the bar, what we were talking about became, well, quite private.

We were talking about masturbation. We were agreeing with each other that it’s a good thing. We went on to agree that if everyone was more accepting of masturbation, it might cure some of the world’s ills. Like overpopulation and unwanted children. Like STDs.

Then he asked a weird question, “What masturbatory thing would you like, but you can’t do it to yourself?”

Normally, I’d never answer a question like that. I’d be shocked. But the way this conversation had been unfolding, it seemed fine to give him my answer:

“I have this fantasy of being tied down, and have someone rub the palm of their hand over the tip of my erect dick. It’s a feeling I can’t stand, and can’t get enough of, all at the same time.”

“Ah, I know the feeling,” he said, adding, “You know, I’ve always been surprised that with a little oil, the feeling is even more intense than with a dry hand. Plus it doesn’t rub the tip of your penis raw.”

I was glad to have some solidarity. Someone who experienced something like me, and was willing to talk about it. Because, face it, sex with women is great, but there can be something missing. Most women are into kissing, dating, and the whole package. Sometimes a guy just wants to get off. Sometimes a guy wants something weird, that most women wouldn’t understand.

“What do you like?”

“I like my balls massaged. Really hard, like rolfing.”

I knew exactly what he was talking about. While I’m not so much a fan of that, I can enjoy a good, firm ball massage.

He went on to say, “But I don’t care for oral, anal, kissing or any of that.”

I was delighted, because that describes me to a tee.

They got the airplane fixed and we boarded, but not before exchanging phone numbers.

A day later he called. “When can we get together?”

I knew exactly what he was talking about.

“Dude, I’m available right now.”

Fifteen minutes later found me in his apartment. We did all the things we discussed. It was even better than I could have imagined. He rubbed the tip of my penis so perfectly that not only did I squirm, yell, and carry on, I even involuntarily let out a little pee a couple of minutes before cumming.

I squeezed his balls so hard I thought they’d pop. He informed me that they are like chicken gizzards. Rubbery. You can’t pop them with your fingertips. You just have to be careful not to injure the back sides where the cords attach. I kind of knew that, but it was reassuring to hear. He was yelling, he was wincing, he was loving it. He kept wanting me to squeeze harder. It kept me very erect doing that to him.

He came without me even touching his penis. Then, he offered the same treatment to me. I had to ask him to be gentler, but found myself very much enjoying the testicle massage. I came a second time, but only because he let go of my scrotum, slowly buried a finger deep in my rectum, and jerked me off with his other hand.

We meet up every month or two. Most of the time we are happy with ourselves or the various ladies we meet. But every now and then, we want something really intense, and we know exactly how to give it to each other.

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Cum Forced Backward

He is around 38 years old, white, medium height, slightly thinner than average, keeps his hair short, shaves most of his light body hair including his genital area, and works in the high-tech industry. He has a girlfriend, and I am married.

His girlfriend seldom ‘puts out’, and my wife says her hormones have shifted, so she’s no longer interested in sexual activities. So, he and I, although we don’t think of ourselves as gay, enjoy playing with each other very much.

We don’t kiss, do blowjobs or any of that. We just like our mutual masturbation.

He likes it rough, and sometimes I do too. We generally edge each other for an hour or so, then one of us goes too far and cums. The other then receives some more attention until he ejaculates also.

I particularly like ball massage, and glans rubbing. That’s when someone, male or female, rubs the palm of their hand over the tip of my dick. Oddly, the sensation is stronger with oil than dry. This glans rubbing business is hard to take. At first it makes one squirm and want to get away, but in a while, it transmutes into a combination of gonna cum or gotta pee feeling that is quite delicious and can keep one on the edge for quite a while.

My friend likes to be fisted, and I’m happy to do that for him from time to time. We have also experimented with sounding. I once worked a length of sterilized aquarium tubing all the way into his bladder. He orgasmed with the tube all the way in, and nothing came out. The ejaculation was blocked by the tubing.

The other night, as I was rubbing his rock-hard penis, and keeping him just below the threshold of cumming, we started talking about that ejaculation that was blocked. He said it was particularly enjoyable and seemed to last longer than the typical orgasm. I have experimented with blocked ejaculations a few times, and found the orgasms did last longer than usual.

I proposed that I might try something I have fantasized about, but would be too chicken to have it done to me. He is more adventurous than I am, and does rather like the rough stuff. I said could bring him to orgasm, and hold it inside by squeezing the tip of his penis. Then, after he came, since he likes various forms of post-orgasm stimulation, I would try to milk him backward. Starting from the tip of his penis which would still be held closed, I’d squeeze farther and farther down his shaft, forcing the sperm backward. I’d continue pressing past his balls, down as far as I could reach to the base of his penis, even reaching my fingers into his asshole if necessary, until the ejaculate was squeezed all the way into his bladder.

He was very enthusiastic about the idea. So, we proceeded. With this exciting new idea, he grew even harder, and came back to the brink of orgasm, where he had already been several times during the past hour. But this time, I kept going, and as his orgasm started, I did pinch the tip of his dick. But it was hard to get a good grip. My fingers wanted to slip off due to the oil we had been using. I tried to get a better grip without losing the grip I had. I didn’t want any sperm to leak out. It seemed like his orgasm was lasting longer than usual, and sure enough, I just couldn’t maintain a good grip between my thumb and the side of my forefinger, and a squirt of semen shot into the air. It was under pressure, so it shot a good three feet!

I quickly got a better grip just below the tip with my other hand, and at that point, I noticed something quite weird: He was still orgasming and the contractions were very, very strong. It was quite obvious. I could feel his dick pulsing strongly in the one hand, and my other hand, which had been pressing lightly on the spot just ahead of his anus felt convulsions there too. I had placed my hand on that perineum area expressly for the purpose of feeling his pulsing orgasm, and was rewarded with some remarkably strong pulses. But not just a few. He kept going and going. I was quite surprised that he was still orgasming.

As I was noticing all that, my grip was slipping again, and another squirt of sperm escaped, and shot well into the air again, landing in sprinkles against his stomach. WTF? He was still orgasming! I tried improving my grip, but didn’t get it right, and yet another squirt slipped out. Finally, I got a good grip, and after what had been probably a full minute, his orgasmic contractions weakened and subsided. Needless to say, we were both quite amazed.

I have had a lot of masturbatory experience in my life, and I’ve never seen anything like this. In all my experiences at the San Francisco Masturbate-A-Thon, SF Jacks, male tantric massages in Berkeley, the Power Exchange, and all sorts of experimentation with friends of both sexes, I have never seen a male orgasm last anywhere near as long as this one did, and have never seen such strong contractions.

I don’t know if it is something specific to my friend, or whether it could be like that for everyone who has an ejaculation blocked in just the right way. I certainly want to find out, and will be experimenting further.

Unfortunately, I had lost a good bit of the sperm I had hoped to trap, but there was still some in his urethra. Perhaps if I had trapped it all, the orgasm would have lasted longer, and been even stronger. I started the process of squeezing it back toward his bladder, and did my best, squeezing down and down. Past his balls. Around the bottom area under his balls, and finally into his asshole. I don’t really know whether I managed to actually move any sperm back or not. And don’t yet know whether I was able to get anything actually into his bladder.

I’m going to ask him next time I see him, probably in a few days. But better than that, I’m pretty sure he’ll want to try again. This time, I’ll make sure to get a better grip, so I can trap all the sperm, then there will be enough to tell for sure whether it is being forced back into his bladder. I might have him do it to me, too.

You might enjoy a similar memoir: Cum Blocking Friend.

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Unexpected Bisexual Exposure

I met a woman who I found quite attractive. We were both 26 years old. She and I became friends, but nothing more. When I tried to expand it to a sexual relationship, she told me not only that she was lesbian, but lived with her girlfriend. She was kind about it, and we remained friends.

I told her that I admired her openness about her lesbianism, and mentioned that I am bisexual, although I was quite closeted about it at the time.

One day, she invited me to dinner with her girlfriend. I kind of knew something was brewing, but didn’t quite know what. When I arrived, it was her, her girlfriend, me, and they introduced me to Gary, and attractive nineteen-year-old kid.

After dinner, and a long, enjoyable conversation well into the evening, the two women told us two guys that we were free to stay over, that we could sleep on the floor of their living room. They gave us blankets and pillows. Gary and I bedded down about six feet away from each other on the thick carpet.

Shortly after the two women went upstairs, Gary scooted up next to me and said something like, “So, you want to fool around?”

I didn’t need an engraved invitation. Within a minute, he had put his hand in my underpants, and I responded in kind, finding his already erect penis under the blanket by feel. Within 15 seconds he kind of curled up, and pushed my hand away. I felt wetness on my fingertips.

The poor fellow had ejaculated just that quickly. That was the end of our fooling around that evening. I realized he wouldn’t be in the mood to finish me, and frankly, I wasn’t in the mood to do anything more anyway. We fell asleep.

In the morning, the four of us had a nice breakfast, then the women and I went off to work, while Gary went to his college class.

The four of us never hooked up again, although we’d see each other around town from time to time, wave, smile, and say “Hi!”

The take-away for me was that it’s really easy to hook up with guys – or girls. Somehow, after that, I was much less reluctant to hide my bisexuality, and as a result, I’ve had many good casual and some long-lasting relationships with people of all sexes.

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Tough Guys (And Girls) Club

The first few days of high school were confusing, as I suppose it is for most kids. This was a huge inner city school, full of kids of all colors, but I wasn’t afraid even though I was small for my age. The school had a reputation for being ‘safe.’ Plus, it didn’t hurt that my mom is a martial arts instructor. She works for big corporations, teaching women tricks to avoid and overcome attacks. From as far back as I can remember, she and I have enjoyed ‘playing,’ which was really me being taught self-defense.

None of that mattered to me. I was fourteen years old, and the only thing on my mind was girls, and jerking off, probably in the reverse order. I jerked off at least once a day, and on one day, I had wanked five times. I loved my dick, and dicks in general. Not in a gay way – I think – but just was interested in how other boys jerk off, what they feel and so on. Oh, I looked at the internet. Who doesn’t? I saw the smooth women with big tits, and that would always send me into ejaculation in no time! What can I say? I’m a big tits guy.

About a week after school started, I saw a big guy smash a smaller guy up against a locker, and throw some significant cuss words at his victim. I couldn’t help myself. As the big guy was raring up to bash the little guy again, something happened to him causing him to fall on his face. That something was me.

He got up, and started aiming for me. Now, I was scared. He was at least 50 pounds heavier than me, and had that bully look in his eyes. I wasn’t sure I’d be able to handle this. He came toward me as I was frantically reviewing in my head all the moves my mom had taught me, trying to figure out what to do. He swung his big arm, fist closed, as I cringed. The blow never came. An even bigger guy had grabbed the bully in a bear hug, saying, “Not today.” The bear hug turned into a throw, as the bully was tossed thirty feet down the hallway.

I thanked the big guy who may have saved me from a bad situation. His said his name was Jason. He seemed uninterested in me, just saying,”You’re welcome,” before walking away into the crowded hallway.

A few days later, in another crowded hallway between classes, I interceded in another altercation. Two girls had gotten into a fight, and fifty other kids formed a circle around them, just watching. Well, not just watching. They were taunting and egging the two girls on. It was really quite vicious. Without thinking it through, I pushed through the crowd, and broke the two girls up, being careful not to get hurt with wild grabs and punches myself.

Soon after, I found myself breaking up yet a third fight. I once again had to apply some of the things Mom taught me to avoid getting hurt and to make sure the bully was stopped. I’m sorry to report he got a black eye out of the deal. Someone asked how I did what I did. I just said, “My mother taught me Judo.”

That afternoon, a big guy came up to me, telling me his name was Nick. He seemed friendly, but I was wary. He could be another bully trying to pick on a smaller kid. He asked me whether I thought I was a “tough guy.”

‘Oh, oh,’ I was thinking. He wants to start something. I said, “No, I’m certainly not a tough guy.”

“I think you are.”

Fuck. I was becoming worried. Not that I couldn’t probably take this guy out with martial arts, but even when you win, you lose in such situations. First, I might get physically hurt. But also, I could get punished by the school, or would start being picked on by other bullies who thought I was a fighter.

Perhaps noticing my expression, he quickly added, “I’m sorry, I didn’t mean to scare you. I was actually sent to invite you to something.”

I was remembering the TV series Glee. I was literally thinking he was going to try to get me to join the glee club, or the chess club or something.

It turns out he wanted me to join the Tough Guys Club. He explained that there’s a group of guys in the school that defend against violence. It’s been a tradition in the school since 1975. That’s the reason this school is known as safe. The club isn’t exactly secret, but they do keep a low profile. He also explained that while most of the ‘tough guys’ are juniors or seniors, they could use me. They thought I could teach them the techniques they saw me use in the fights.

I was doubtful, but he talked me into attending a meeting. When I accepted, he hesitated a moment, then blushing, he said, “But there’s one thing: we meet Roman style.”

“Huh?”

“In ancient Rome, the men got together in what were called ‘baths.’ There they discussed the events of the day, they played games, and they had a good time.”

“So?”

Again he hesitated. Then he blurted out, “They were naked.”

“And so?”

Oh! I got it! These tough guys meet naked! A flood of emotions came over me. I had always wanted to be with a group of naked people. I had jerked off many times imagining myself in orgies, in circle jerks, being watched by a crowd while fucking, and so on. A group of naked guys, how cool was that? I mean, it would be even better if it were a mixed group, guys and girls, but this could be absolutely exciting in its own right. But then some sort of fear came over me, too. This was very weird, right?

So there I was, facing a decision. Right then and there, I could decline, and be saved from whatever weirdness this invitation might involve. But then, I’d miss out on what I thought was the biggest and best opportunity of my young life. I smiled at him, and accepted.

Thursday afternoon I was invited to Jason’s house. I explained I had no way to get there, and it was a long walk. Between classes, a big guy I hadn’t met came walking right up to me, then passed me a note. It said, “I’ll drive you there and back.” His name, Kevin, and phone number was on the note.

Between classes, I called my mom, and asked her if I could come home late, explaining I was trying out an after-school martial arts club. She was delighted.

I was nervous on the ride over. I asked Kevin questions about the Tough Guys Club. He was mostly talking about the history, like how they started over 40 years ago, and that the tradition had been passed down year after year. He said the school officials stay uninvolved because they know it’s a good thing, but they can’t endorse it – you know, possible lawsuits and things.

I tried to ask about the nudity and all, but I didn’t find out any details. Again that term, “Roman” came up, then he went back into history, telling me about how other inner city schools had riots and things, and how the academic standard was higher here, due in no small part to the Tough Guys.

Part of my nervousness was natural. Who wouldn’t be all freaked out about taking your clothes off with a bunch of other people? But part was due to my development, or lack thereof. I had like five or six scraggly hairs on my crotch. That’s all. I knew they’d grow in eventually, but at the moment, I looked like a child. My neighbor, on the other hand, had a full forest of hair at age eleven. Go figure!

We got there. There were twenty kids, all big kids, except me, crowded into Jason’s living room. His parents both worked evening shifts at the hospital, so the house was all ours. He explained that the parents knew about the Tough Guys Club, and supported it. In fact, his father had been a member twenty-some years before.

Two of the boys were already undressed. Fully naked, sitting on a sofa. Oh, my god: One of them was sporting a boner! He seemed oblivious, like sitting naked in a room full of boys with a boner was the most natural thing in the world. The other guys were equally unconcerned – like it was no big deal to have an erection in the group.

Everyone was talking about everything as the boys were undressing. I kind of hung back a bit taking off only my shirt. Somehow, my reputation had preceded me. Several guys came up to me asking questions about martial arts. They seemed genuinely interested, and more, they were downright friendly. Inviting. Acting as if I had always been a part of their family or something.

Now, most of the guys were fully naked, and here I was still only shirtless. I knew what I had to do. Otherwise I’d be embarrassed as a prude or something. So, I took off my clothes. When in Rome… right?

They had pushed the furniture out of the way in the large, deeply carpeted living room, and covered the floor with plastic sheeting, then bed sheets and large towels. These big kids started mock fighting. Some were throwing punches, some were wrestling. More than one was fully erect. I was delighted, but still a little scared. My heart was racing. Just what I was scared of, I don’t know. I don’t think it was that I was small and nearly hairless in a sea of big hairy guys. I think it was just the newness of the situation. For whatever it’s worth, not one of them said anything about my underdeveloped nature. I mean, they could have teased me endlessly about that. On the other hand, they could have teased the erect ones about being ‘gay’ or something. But there was no teasing at all.

Still, I was willing myself not to become erect. I somehow figured that would be a bad thing. As I was watching the fighting, I was thinking to myself, ‘It’s too bad they don’t know what I know. They’re being terribly inefficient. They’d be so much better at this if they knew a few of the moves my mom taught me.’

After watching ten minutes of all this fake fighting and tussling around on the floor, one of the guys tried to tackle me. Suddenly, I was involved in the fun free for all. Because he was large, I focused, and I guess I rolled him a little too hard. He said, “Oomph,” as he hit the floor. I didn’t hurt him, and he came up laughing. He asked, “How did you do that?”

Suddenly, no one was wrestling any more. Everyone was looking at me. Kevin, seemingly the leader of the group, asked, “Will you show us?”

I felt like a fucking movie star in that moment. A naked movie star, but still a star. This was my moment. All these big, amazing, friendly guys, and they wanted something from me. Something I could give them!

For the next hour, I was showing them some basics, and they were practicing on each other. The erections had all subsided. This was serious but fun business. The nakedness normalized in my mind. Odd, I know, but it was as if we were naked as God created us, and it was all just fine.

Kevin called for attention. Everyone stopped what they were doing and sat down on the sofa, chairs or on the floor. “Now it’s that time of the day we’ve all been waiting for. Triple-T, Tough guy Toughness Testing.”

I wasn’t sure I liked the sound of Triple-T. It sounded like something painful, or something that I’d be able to do only painfully. I was imagining arm wrestling. It was probably going to be something like that.

For my benefit, Jason explained to the group. “As you all know, we need a way to bolster our toughness. Our resistance to pain. But we don’t want to suffer pain or risk injury in the process. Forty years ago, the founders of the club came up with a technique that fits the bill so perfectly, we still practice it today. Glans rubbing.”

I didn’t know what a glans was, but I was pretty sure ‘rubbing’ something wasn’t going to be good. Now, I wasn’t sure I should be here. But everyone was smiling. They weren’t looking like they were going to undergo some kind of test, some kind of ordeal. Oh, and something else, at least half of the kids were erect!

Before I could figure anything out, the guys started pairing off. It turns out there were an odd number of us, so I just sat there wondering what was going to happen. It took only seconds to find out.

In each pair of kids, one laid down on the sheets on the floor, and the other knelt before him. Here comes the shocking part: The kneeling guys grabbed the laying down guys’ dicks, and started putting massage oil on them. Right on their dicks! Most of the guys were hard. Those that weren’t were getting gentle little handjobs to get them erect.

Soon, everyone laying down was erect. Most of the guys kneeling or sitting next to them were also erect. What a sight to behold!

One of the sitting guys leaned over and clicked something on his phone. “OK, three minutes,” he announced.

The kneeling or sitting guys were holding the laying down guys’ dicks with one hand wrapped around their shafts. At the three-minute announcement, they began rubbing the oiled palms of their hands over the tips of the laying down guys’ dicks.

Everyone on the floor was squirming, moaning, yelling and laughing. I had no idea what they were feeling, but it was certainly intense. This went on and on. I’m sure I don’t need to tell you I had a rock-hard erection just watching this.

Toward the end of the second minute, the yelling and squirming settled down somewhat. The guys were calming down. One of the guys started grunting, and ejaculated, right there in front of me.

It was all I could do to not start masturbating right there.

Ding. The three-minute timer went off. There was a sigh of relief throughout the room.

The laying down and sitting up people changed positions.

I would have been content to just keep watching. I knew I’d be wanking big time the minute I got home after witnessing this. But a guy came over to me and said that I shouldn’t be left out of the fun. I couldn’t have agreed more.

I took my position on the floor.

“Three minutes” was announced.

My big guy started gently rubbing my rock-hard, but little cock. At the very moment he started, it was nearly unbearable. I had no idea! I’m sure you, dear reader, have experienced this, but I hadn’t until then. What a crazy tickle. Not pain, as you know, but un-fucking-bearable. But kind of sexy, too. I knew what I had to do. I had to lay there and take it.

Now, I suppose I could have refused, or gotten up off the floor or something, but I knew that would mark me as a sort of looser. I’ll bet these guys would have accepted that, but there was no way I’d give up. I had to handle it, no matter what.

And it was hard – I mean difficult. I was hard, erect as I had ever been in my life, and in terrible anguish. Yet, wonderful anguish, if that makes any sense. Pretty soon, the feeling shifted. It wasn’t quite as unbearable, and started to feel like I was going to involuntarily pee, or ejaculate – at the same time. I had never felt such a thing.

Now, the ‘gonna cum’ feeling was building up more and more, but I still had to pee, too. I was going to ejaculate. There was nothing I could do about it.

“Ding.”

The big guy let go of my penis. I was so close to cumming that it actually pulsed a couple of times, but nothing came out.

We switched roles. Now I was sitting next to my big guy. Three minutes was announced, and I went to work. It was the first time I had wrapped my fingers around such a big cock. It felt amazing. I hadn’t realized how warm another guy’s penis could be. How soft the skin was, and how hard it was inside. As I started in on the glans rubbing. His face contorted all up, he squirmed, he moaned, but he didn’t quit on me. No, instead, he ejaculated all over my hands. I was delighted to see so much cum. It was thick and white, and there was a lot of it. Not clear and just a couple of drops of clear liquid like mine. I looked forward to the day when I could cum like that.

All in all, it was the best afternoon of my life.

We met every Thursday, and I was always so up for it, literally. Sometimes I’d end up ejaculating, mostly not. Some of the guys let out involuntary streams of pee. That was always problematic, because we could not, absolutely could not, get anything on the carpet. The sheets could soak it mostly up, but still, we had to be careful.

In time, I grew bigger, topping out at 5’11” with a reasonable six-inch penis, and a nice forest of hair on my crotch. Perhaps to make up for my late start, I grew a mustache, then a bit of a beard when I was only seventeen.

One day started out like all the others, but then Jason wanted to discuss something. The group was considering a girl. Suki was her name. She was of Samoan descent. She was rounded but not fat. She was also quite tall. She was a fighter, but always as a defender, not an instigator. She was a good fit for the club, other than being female.

I was all in favor of adding females. My heart was racing, thinking about having a naked girl among us. I was wondering how a girl would participate in glans rubbing. We had a vote. To my astonishment, it was unanimous, even the outspokenly gay guys were in favor. I suppose it does make sense. Why on Earth would we exclude females if they could be ‘tough guys’ also?

The first meeting with Suki was awkward at first. We all kept all our clothes on. Fortunately, Suki is a gregarious individual. She simply said, “I know you guys all get naked. Don’t let me stop you,” and with that, she lifted up her T-shirt revealing that she wasn’t wearing a bra. Her pendulous brown breasts with jet black nipples were amazing. I couldn’t get my clothes off fast enough. Same with the other guys. Everyone was naked within a minute, even Suki. She was beautiful – I mean to me. Some might say she was too heavyset, but I wasn’t complaining! She also shaved her crotch hair, as did some of the guys. Pretty much all the guys, including the gay ones, were erect. Maybe their erections were due to seeing their male buddies reacting to this female. I don’t know. I was just happy to be here in heaven.

We wrestled for a while. There were more erections than normal. Suki took it all in stride, as if play fighting with naked and erect guys is just another ordinary activity.

Then it was time for the Triple-T. No one knew quite how to proceed. There was a long moment of awkward silence.

Suki broke the silence. “Now, from what my brother has told me,” Suki began, quickly explaining that he didn’t tell her anything about the ritual until after she had been confirmed as a member, “you guys have some sort of test…”

One of the guys started telling her the details. He was blushing severely. She interrupted him. “I already know, I’m all in.”

“Now, I can’t speak for all women, but I don’t think we have an exact equivalent of glans rubbing. However, after we orgasm, there is such a thing as too much clit rubbing. I think that may be similar. I’d love to experience that.”

I just can’t tell you how lucky I was to be paired with Suki that day. I was the first ever to rub her to multiple orgasms, and then keep going, causing her to moan, squirm and scream with the rest of us.

When it was my turn, I came almost immediately. I really tried not to, but the moment her hefty fingers wrapped around my penis, I knew the effort was useless. I ejaculated within the first thirty seconds. She was delighted, claiming this is the first time she had seen sperm in person. She cautiously licked some from her fingers, said ‘yum’ and then licked more off her hand.

By the time I had graduated from high school, the tough guys were almost half female. The school won a national award for being the school with the least number of violent incidents.

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Topless in Buffalo

I have always felt that it is unfair that men can go topless on a hot summer day, and women can’t. How weird is that? Well, I’m a woman, and I always wanted to know what it feels like to go topless, to feel the wind on your chest, to get an all-over tan. And, I have a distinct advantage: Small boobs. I’m not quite flat-chested, but close. And, that’s never bothered me, and certainly hasn’t hurt my sex life. Several guys and girls I have been with say they find my little pancakes with a mint on top absolutely attractive. OK, I’ll go with that:) My current girlfriend has large, pendulous breasts, and I love that. Go figure.

Topless with small breasts (tiny tits) in Buffalo, New York

Over weeks, months really, I hatched a plan. I patiently waited until today, the first hot summer day in Buffalo, New York, 87 miles from where I live. I had cut my somewhat unruly hair short two weeks ago. It was short for a girl, but would be considered just a bit longer than typical for a guy. In fact, my hair kind of looked all crazy, like Einstein, but not gray. Being part-Asian, my hair is black.

Yesterday, I bought some men’s shorts, and a very masculine T-shirt with a beer commercial on front. I got some men’s shoes, and some of those athletic socks they wear, which us women seldom wear. Finally, I needed a new bike helmet. Pink would be a dead give-away, so I found a black one at a thrift store for $4.

I changed into my new clothes, leaving my ridiculous bra off. I call it ridiculous because I’ve never needed it. My small breasts do not sag. I just wear a bra because that’s what we girls do. But not today.

I left the hotel room dressed as a guy, unloaded my bike, checked the air pressure in the tires, and got on. I started to ride through the neighborhood, and soon I was downtown. It was hot, and I was already sweating pretty well. So, being the guy that I was today, I took off my T-shirt and tucked it into my handlebar pack. No one looked up. After all, I really looked like a guy, maybe just a guy who is kind of pudgy on top. The cars just kept passing by. The pedestrians were all business-as-usual. But was I nervous? Hell yes!

I started to ride, and for the first time in my adult life, I felt the wind whistling gently past my chest, my whole chest, as I rode along. I felt the sun beating down on my back. It all felt so beautiful, my eyes teared up. But, guys don’t cry, so I held it back, and kept riding through temporarily bleary eyes.

All in all, I rode five miles through the streets of downtown Buffalo. I kept looking for recognition. Oh, I knew no one would recognize me. Plus, just to be sure, I was wearing my helmet and sunglasses. That’s why I came to a place 87 miles away. But I was waiting for someone to say, “Hey, she’s a girl, and she’s topless!” It never happened. Everyone mistook me for a guy.

I figured my back had received as much sun as was good, so it was time to go back to the hotel room. Now I can’t explain why that experiment made me so horny. Perhaps it was feeling the fresh air on my body. Perhaps it was being almost naked in public. But the minute I got in the door, I threw off my helmet, shoes, socks and shorts, and my hands were all over my nipples and clit. I orgasmed in seconds, and then several more times during the next half hour.

I don’t know if I’ll ever do the experiment again, but maybe. Maybe I’ll even go a step further – totally nude. I might like to try a nude beach someday. For that, I won’t have to disguise myself at all. Hmmm. Interesting.

I want my hair to grow back. The whole thing feels kind of embarrassing now, and my hair is a reminder. When people ask about my short hair, I won’t tell them about the experiment. Instead, I’ll just say I wanted to try a low-maintenance cut. This evening, my girlfriend wanted to know where I was today. When reluctantly I told her what I had done, she started licking my vagina with remarkable vigor and I came several times.